An efficient iodine(III)‐based protocol for the chlorination and catalytic nitration of N‐tosyl anilines as well as the proposed reaction mechanism is described. The synergistic combination of the commercially available [bis(trifluoroacetoxy)iodo]benzene (PIFA) with AlCl3, or (PhIO)n with Al(NO3)3, allowed the electrophilic introduction of chlorine and nitro group in the N‐tosyl aniline core in non‐acidic conditions. Our DFT calculations, performed for the chlorination process, indicate that this occurs through a cationic pathway in which the [Cl‐PhI
OTFA⋅AlCl3] is the chlorinating species and is formed under neutral conditions.
A novel bis‐heterocyclic system encompassing the 1,2‐dihydro‐3H‐pyrrolo[3,4‐b]indolizin‐3‐one and 1,5‐disubstituted tetrazole moieties was designed, synthesized, and evaluated as a Copper (II) recognizing agent. This was achieved by exploiting the optical characteristics of indolizine and the copper recognizing activity of tetrazoles. For the preparation of these compounds, a novel and simple synthetic strategy consisting in a double one‐pot process involving four‐step reactions was developed. The first process is a one‐pot five component reaction by using propargylamine as a bifunctional reactant to access the key intermediate, the N‐acylated tetrazole. Consequently, N‐acylated tetrazole was subjected to a one‐pot three component reaction, consisting in a bimolecular nucleophilic substitution followed of a domino process to afford the target compounds. The photophysical properties of the obtained bis‐heterocycles were evaluated against copper (II) addition.
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